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ARCHIVE:  March 14, 2002

Trimethoxylated Amphetamine Derivatives

Dear Dr. Shulgin:

In your inquiry into the 2,4,6-trimethoxy substitution pattern, did you have any reason to suspect that this might be a doorway to something new? I have found TMA-6 to be an interesting compound to say the least. Please make any comments you can on this, for me. Thank you.

-- Observer


Dear Observer:

Early in my studies, that doorway was pretty well closed. In the making of all six possible trimethoxylated amphetamine derivatives, the remarkable potency and activity of the 2,4,5- substitution pattern (of TMA-2) completely captured my attention. And the endless variations of these substituents led to treasure after treasure, with 4-position ethers (MEM, MPM), alkyl groups (DOM, DOET), halides (DOB, DOI) and on and on. This then led back to the corresponding phenethylamines with many more gems, but always with the 2,4,5-trisubstitution pattern.  

But the last of the six possible trisubstituted amphetamines was the 2,4,6-trimethoxyamphetamine compound, TMA-6. I had made it way back there early, but had been totally seduced by TMA-2. It was quite a few years later that I realized that TMA-6 was a true doorway that could open up to a world completely analogous to the one that was part of TMA-2. Anyone who might want to explore it would surely find similar treasures with the 4-position ethers, alkyl groups, halides, and on and on. I made a few of them and they were completely real. Different, yes, but fascinating. Here was a truly parallel universe waiting to be discovered by a curious chemist.

But I was destined not to be that person! I had become deeply involved in the miracles of the tryptamines and knew I would have to leave that unexplored path of the 2,4,6-substituted compounds to someone else. It is truly a virgin world of unknown things.

-- Dr. Shulgin

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